SE466206B - Foerfarande foer utvinning av ceftazidim ur en vattenhaltig loesning - Google Patents

Foerfarande foer utvinning av ceftazidim ur en vattenhaltig loesning

Info

Publication number: SE466206B
Authority: SE; Sweden
Prior art keywords: ceftazidime; water; solution; process according; resin
Prior art date: 1984-03-09

Application number

SE8501170A

Other languages

English (en)

Swedish (sv)

Other versions

SE8501170L (sv

SE8501170D0 (sv

Inventor

T W Stone

C Robinson

D G Hughes

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-03-09

Filing date

1985-03-08

Publication date

1992-01-13

1985-03-08 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1985-03-08 Publication of SE8501170D0 publication Critical patent/SE8501170D0/xx

1985-09-10 Publication of SE8501170L publication Critical patent/SE8501170L/

1992-01-13 Publication of SE466206B publication Critical patent/SE466206B/sv

Links

238000000034 method Methods 0.000 title claims description 24
239000007864 aqueous solution Substances 0.000 title claims description 13
229960000484 ceftazidime Drugs 0.000 claims description 55
NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 claims description 55
239000000243 solution Substances 0.000 claims description 48
229920005989 resin Polymers 0.000 claims description 34
239000011347 resin Substances 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 13
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 10
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
239000003480 eluent Substances 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 8
238000010828 elution Methods 0.000 claims description 7
229920001577 copolymer Polymers 0.000 claims description 6
239000011148 porous material Substances 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
238000004128 high performance liquid chromatography Methods 0.000 description 11
239000012535 impurity Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
239000007787 solid Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
239000002253 acid Substances 0.000 description 5
229920001429 chelating resin Polymers 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000001179 sorption measurement Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
-1 Amberlite XAD-2 Chemical compound 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229920002125 Sokalan® Polymers 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000004686 pentahydrates Chemical class 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000003109 Karl Fischer titration Methods 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000012958 reprocessing Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000008351 acetate buffer Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000000711 polarimetry Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SE8501170A 1984-03-09 1985-03-08 Foerfarande foer utvinning av ceftazidim ur en vattenhaltig loesning SE466206B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB848406218A GB8406218D0 (en)	1984-03-09	1984-03-09	Process

Publications (3)

Publication Number	Publication Date
SE8501170D0 SE8501170D0 (sv)	1985-03-08
SE8501170L SE8501170L (sv)	1985-09-10
SE466206B true SE466206B (sv)	1992-01-13

Family

ID=10557840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8501170A SE466206B (sv)	1984-03-09	1985-03-08	Foerfarande foer utvinning av ceftazidim ur en vattenhaltig loesning

Country Status (22)

Country	Link
US (1)	US4769450A (de)
JP (1)	JPH0645626B2 (de)
KR (1)	KR890001010B1 (de)
AT (1)	AT386206B (de)
AU (1)	AU581427B2 (de)
BE (1)	BE901900A (de)
CA (1)	CA1239391A (de)
CH (1)	CH664156A5 (de)
DE (1)	DE3508372C2 (de)
DK (1)	DK157028C (de)
ES (1)	ES541085A0 (de)
FI (1)	FI85488C (de)
FR (1)	FR2560879B1 (de)
GB (2)	GB8406218D0 (de)
IE (1)	IE57953B1 (de)
IL (1)	IL74456A (de)
IT (1)	IT1182717B (de)
NL (1)	NL194238C (de)
NZ (1)	NZ211363A (de)
PT (1)	PT80081B (de)
SE (1)	SE466206B (de)
ZA (1)	ZA851767B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4954624A (en) *	1986-10-07	1990-09-04	Sandoz Ltd.	Process for the production of cephalosporin derivatives
TW553946B (en)	1999-09-08	2003-09-21	Fujisawa Pharmaceutical Co	Method for separating lactone-containing high-molecular weight compounds
EP1312387B1 (de) *	2000-08-25	2014-05-21	Kaneka Corporation	Verfahren zur entfernung bakterieller toxine aus einem bakterielle toxine enthaltenden medium
WO2002017945A1 (en) *	2000-08-31	2002-03-07	Hauser, Inc.	Efficient method for producing compositions enriched in anthocyanins
CN102875576A (zh) *	2012-10-31	2013-01-16	苏州致君万庆药业有限公司	一种抗菌素头孢他啶的合成、注射用头孢他啶及其制备方法
CN102924483B (zh) *	2012-10-31	2015-06-17	海南合瑞制药股份有限公司	一种头孢他啶晶体化合物、其制备方法及其无菌混合粉形式的药物组合物
CN110857308B (zh) *	2018-08-24	2021-02-26	浙江长典医药有限公司	一种注射用头孢他啶的制备方法
CN111196818A (zh) *	2018-11-19	2020-05-26	浙江长典医药有限公司	一种注射用头孢他啶的制备方法
CN109824698B (zh) *	2019-01-23	2020-09-22	华北制药河北华民药业有限责任公司	一种头孢他啶的制备方法
CN111116611B (zh) *	2019-11-21	2021-05-07	华北制药河北华民药业有限责任公司	一种注射用头孢他啶粉针制剂的制备方法
CN113101274B (zh) *	2021-03-31	2022-09-06	海南海灵化学制药有限公司	一种注射用头孢他啶粉针剂及其制备工艺
CN114047271B (zh) *	2021-11-12	2023-03-17	海南葫芦娃药业集团股份有限公司	一种注射用头孢他啶制剂中有关物质的检测方法
CN117700430A (zh) *	2023-12-11	2024-03-15	哈药集团技术中心	一种降低头孢他啶杂质h的工艺方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH541579A (de) *	1969-05-13	1973-09-15	Ciba Geigy Ag	Verfahren zur Abtrennung von Cephalosporin C aus Rohlösungen
BE824028A (fr) *	1974-01-23	1975-06-30		Procede pour la purification de cephalosporines comportant un groupe acide carboxylique libre
GB2025398B (en) *	1978-05-26	1982-08-11	Glaxo Group Ltd	Gephalosporin antibiotics
AR228726A1 (es) *	1978-05-26	1983-04-15	Glaxo Group Ltd	Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato
US4329453A (en) *	1979-10-02	1982-05-11	Glaxo Group Limited	Cephalosporin antibiotic
US4427677A (en) *	1980-12-31	1984-01-24	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds
DE3313818A1 (de) *	1983-04-16	1984-10-18	Hoechst Ag, 6230 Frankfurt	Neue kristallmodifikation von ceftazidim
US4537959A (en) *	1984-03-26	1985-08-27	Eli Lilly And Company	Crystalline cephalosporin antibiotic salt
US4616080A (en) *	1984-07-02	1986-10-07	Eli Lilly And Company	Simplified process of forming crystalline ceftazidime pentahydrate
US4659813A (en) *	1984-11-08	1987-04-21	Eli Lilly And Company	Crystallization process for ceftazidime derivative

1984
- 1984-03-09 GB GB848406218A patent/GB8406218D0/en active Pending
1985
- 1985-02-27 IL IL74456A patent/IL74456A/xx not_active IP Right Cessation
- 1985-03-07 CH CH1042/85A patent/CH664156A5/de not_active IP Right Cessation
- 1985-03-08 KR KR1019850001497A patent/KR890001010B1/ko not_active Expired
- 1985-03-08 FR FR8503451A patent/FR2560879B1/fr not_active Expired
- 1985-03-08 DE DE3508372A patent/DE3508372C2/de not_active Expired - Fee Related
- 1985-03-08 AT AT0070185A patent/AT386206B/de not_active IP Right Cessation
- 1985-03-08 AU AU39670/85A patent/AU581427B2/en not_active Ceased
- 1985-03-08 PT PT80081A patent/PT80081B/pt not_active IP Right Cessation
- 1985-03-08 IE IE608/85A patent/IE57953B1/en not_active IP Right Cessation
- 1985-03-08 NZ NZ211363A patent/NZ211363A/xx unknown
- 1985-03-08 NL NL8500663A patent/NL194238C/nl not_active IP Right Cessation
- 1985-03-08 JP JP60044965A patent/JPH0645626B2/ja not_active Expired - Lifetime
- 1985-03-08 GB GB08506053A patent/GB2157682B/en not_active Expired
- 1985-03-08 ES ES541085A patent/ES541085A0/es active Granted
- 1985-03-08 ZA ZA851767A patent/ZA851767B/xx unknown
- 1985-03-08 FI FI850926A patent/FI85488C/fi not_active IP Right Cessation
- 1985-03-08 DK DK106585A patent/DK157028C/da not_active IP Right Cessation
- 1985-03-08 SE SE8501170A patent/SE466206B/sv not_active IP Right Cessation
- 1985-03-08 IT IT47786/85A patent/IT1182717B/it active
- 1985-03-08 CA CA000476038A patent/CA1239391A/en not_active Expired
- 1985-03-08 BE BE0/214620A patent/BE901900A/fr not_active IP Right Cessation
1987
- 1987-06-18 US US07/063,315 patent/US4769450A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR890001010B1 (ko)	1989-04-18
IL74456A (en)	1988-11-15
DK157028B (da)	1989-10-30
NL8500663A (nl)	1985-10-01
PT80081B (en)	1987-03-25
FI850926L (fi)	1985-09-10
AU581427B2 (en)	1989-02-23
AT386206B (de)	1988-07-25
DE3508372A1 (de)	1985-09-12
NZ211363A (en)	1988-07-28
IL74456A0 (en)	1985-05-31
FI850926A0 (fi)	1985-03-08
KR850006419A (ko)	1985-10-05
FI85488B (fi)	1992-01-15
DK157028C (da)	1990-04-02
SE8501170L (sv)	1985-09-10
NL194238B (nl)	2001-06-01
NL194238C (nl)	2001-10-02
AU3967085A (en)	1985-09-12
GB8406218D0 (en)	1984-04-11
IT1182717B (it)	1987-10-05
BE901900A (fr)	1985-09-09
FR2560879A1 (fr)	1985-09-13
IT8547786A1 (it)	1986-09-08
IE57953B1 (en)	1993-05-19
GB2157682A (en)	1985-10-30
IT8547786A0 (it)	1985-03-08
ES8603495A1 (es)	1985-12-16
GB2157682B (en)	1987-08-26
US4769450A (en)	1988-09-06
ZA851767B (en)	1986-11-26
SE8501170D0 (sv)	1985-03-08
JPH0645626B2 (ja)	1994-06-15
DK106585A (da)	1985-09-10
ATA70185A (de)	1987-12-15
FR2560879B1 (fr)	1987-05-22
FI85488C (fi)	1992-04-27
PT80081A (en)	1985-04-01
CH664156A5 (de)	1988-02-15
DE3508372C2 (de)	1995-05-04
DK106585D0 (da)	1985-03-08
ES541085A0 (es)	1985-12-16
GB8506053D0 (en)	1985-04-11
CA1239391A (en)	1988-07-19
IE850608L (en)	1985-09-09
JPS60252484A (ja)	1985-12-13

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